Hydrochloric Acid → 1-(8-Hydroxy-5-methyl-7-quinolinyl)ethanone

HRID 1192560

반응식

HRID 1192560 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl-].[Cl-].[Cl-].[Al+3].[C:17](Cl)(=[O:19])[CH3:18].Cl.[OH-].[Na+]>O.ClCCl>[OH:12][C:9]1[C:10]([C:17](=[O:19])[CH3:18])=[CH:11][C:2]([CH3:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 712085-Methyl-8-hydroxyquinolineHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 190434591-(8-Hydroxy-5-methyl-7-quinolinyl)ethanone

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 5-methylquinolin-8-ol (5.91 g, 37.1 mmol, from ChemBridge), aluminum trichloride (20.00 g, 150.0 mmol), and acetyl chloride (12.1 mL, 170 mmol) was stirred at 0° C. for 4 hours, then heated at 130° C. for 12 hours, cooled, and decomposed with water (39 mL) (caution! with external ice-cooling if necessary) and conc. HCl (13 mL). The precipitate was filtered, and dried under reduced pressure. The solid obtained was then dissolved in 50 mL of water. To the solution was added 100 mL of dichloromethane. The mixture was cooled with an ice bath and the pH adjusted to 4 with slow addition of 20% NaOH. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine and dried over sodium sulfate. The suspension was filtered through a plug of cotton and concentrated to dryness. The residue was used directly in the next step (5.8 g, 78%). LCMS calculated for C12H12NO2 (M+H)+: m/z=202.1; Found: 202.0.

후처리

  1. temperatureheated at 130° C. for 12 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. customdried under reduced pressure
  5. customThe solid obtained
  6. temperatureThe mixture was cooled with an ice bath
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. washThe combined organic layers were washed with water, brine
  10. dry with materialdried over sodium sulfate
  11. filtrationThe suspension was filtered through a plug of cotton
  12. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-fda3c65bbef748bcb621dd751cbffa39
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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